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So basically, you are being invited to connect a USB device from an unknown source, with unknown code on it, to your machine. There have been many instances of people leaving USB sticks with exploit binaries around for people to find. You find the stick, stick it in your machine, and are promptly exploited. Regardless of whether the creator of the dead drops hasn't done this intentionally themselves (hopefully, they haven't), you have no idea what might have been placed on the sticks by others.

Hate to break it to you, but the first thing a Windows boxen will do when it is then plugged into the drive then will be prompt the user to format it, NTFS, sort of making this hardly any real fix, and really just more annoying to the projects spirit as whatever pdf of the Anarchist's Cookbook or whatever "contraband" files these kiddies will be spreading at these dead-drops will be deleted twice.

You ultimately don't have to connect to the USB stick if you don't want to. And as for your suggestion, you've obviously missed the point, because the concept behind it is NOT to share files with someone you know. But rather to create drop spots in an urban environment to see what happens. Think of it as creating a parallel (and sllightly subversive) infrastructure that people might use in new and original ways. I would expect that in the age of "oh nohs! all the guvernmsnts r trackingzz us!!!" you would applaud this in a small way. With a bit of encryption you might be able to do all sorts of stuff with it.

But as we say in Art: glad you don't like -- must mean its doing something right.